NPASS Compound

Structure

CID23778 OpenBabel06191715352D 23 25 0 0 1 0 0 0 0 0999 V2000 -0.7326 2.4022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7130 1.0534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1704 2.4539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0451 1.9485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3355 -1.0107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9347 -1.4385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0036 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0038 0.9623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1698 -0.4822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5018 1.4442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8334 1.4448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6681 0.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3359 0.9626 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0002 0.9633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6679 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 1.4445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8336 -0.4816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1702 1.4439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3357 -0.0007 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8340 2.4478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8335 -1.4848 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8338 -0.4812 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 23 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 12 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 13 19 1 0 0 0 0 13 20 1 1 0 0 0 14 16 1 0 0 0 0 14 18 2 0 0 0 0 15 17 1 0 0 0 0 15 20 1 0 0 0 0 16 21 2 0 0 0 0 17 18 1 0 0 0 0 17 22 2 0 0 0 0 18 23 1 0 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	344.632
LogP:	5.423
LogD:	4.292
LogS:	-4.741
# Rotatable Bonds:	2
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.747
Synthetic Accessibility Score:	3.886
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.925
MDCK Permeability:	1.9267245079390705e-05
Pgp-inhibitor:	0.903
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.128
20% Bioavailability (F20%):	0.965
30% Bioavailability (F30%):	0.883

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.12
Plasma Protein Binding (PPB):	99.32247161865234%
Volume Distribution (VD):	4.414
Pgp-substrate:	2.447244644165039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.346
CYP1A2-substrate:	0.96
CYP2C19-inhibitor:	0.315
CYP2C19-substrate:	0.908
CYP2C9-inhibitor:	0.503
CYP2C9-substrate:	0.878
CYP2D6-inhibitor:	0.378
CYP2D6-substrate:	0.179
CYP3A4-inhibitor:	0.445
CYP3A4-substrate:	0.847

ADMET: Excretion

Clearance (CL):	4.042
Half-life (T1/2):	0.201

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.321
Drug-inuced Liver Injury (DILI):	0.079
AMES Toxicity:	0.095
Rat Oral Acute Toxicity:	0.415
Maximum Recommended Daily Dose:	0.542
Skin Sensitization:	0.555
Carcinogencity:	0.513
Eye Corrosion:	0.003
Eye Irritation:	0.603
Respiratory Toxicity:	0.959

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC23778

Natural Product ID:	NPC23778
*Common Name:**	Taiwaniaquinone G
IUPAC Name:	(4bS,8aS)-3-methoxy-4b,8,8-trimethyl-2-propan-2-yl-6,7,8a,9-tetrahydro-5H-fluorene-1,4-dione
Synonyms:	Taiwaniaquinone G
Standard InCHIKey:	AVTKDJHUFWOONG-RBZFPXEDSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-11(2)14-16(21)12-10-13-19(3,4)8-7-9-20(13,5)15(12)17(22)18(14)23-6/h11,13H,7-10H2,1-6H3/t13-,20-/m0/s1
SMILES:	COC1=C(C(C)C)C(=O)C2=C(C1=O)[C@@]1(C)CCCC([C@@H]1C2)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1088628
PubChem CID:	25199270
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	twig	n.a.	PMID[22474975]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31347365]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9014350]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	1
IC50	3

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	EC50	>	10000.0	nM	PMID[536561]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	16800.0	nM	PMID[536562]
NPT2424	Cell Line	T84	Homo sapiens	IC50	=	14100.0	nM	PMID[536562]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	30500.0	nM	PMID[536562]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC23778 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	1595
0.2-0.3	7320
0.3-0.4	16312
0.4-0.5	9082
0.5-0.6	5806
0.6-0.7	2157
0.7-0.8	213
0.8-0.85	11
0.85-0.9	3
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9351	High Similarity	NPC8091
0.8816	High Similarity	NPC283087
0.8608	High Similarity	NPC474085
0.8228	Intermediate Similarity	NPC469996
0.8205	Intermediate Similarity	NPC92080
0.8193	Intermediate Similarity	NPC8518
0.8193	Intermediate Similarity	NPC241512
0.8193	Intermediate Similarity	NPC132228
0.8193	Intermediate Similarity	NPC6185
0.8193	Intermediate Similarity	NPC133652
0.8193	Intermediate Similarity	NPC263997
0.8	Intermediate Similarity	NPC30321
0.7857	Intermediate Similarity	NPC237712
0.7831	Intermediate Similarity	NPC321289
0.7831	Intermediate Similarity	NPC327969
0.7805	Intermediate Similarity	NPC108955
0.7778	Intermediate Similarity	NPC476808
0.7765	Intermediate Similarity	NPC474680
0.7738	Intermediate Similarity	NPC271784
0.7727	Intermediate Similarity	NPC478257
0.7727	Intermediate Similarity	NPC223093
0.7727	Intermediate Similarity	NPC478258
0.7727	Intermediate Similarity	NPC475823
0.7727	Intermediate Similarity	NPC474209
0.7711	Intermediate Similarity	NPC55869
0.7711	Intermediate Similarity	NPC225515
0.7692	Intermediate Similarity	NPC474539
0.7683	Intermediate Similarity	NPC192329
0.7683	Intermediate Similarity	NPC476177
0.7683	Intermediate Similarity	NPC475681
0.7654	Intermediate Similarity	NPC472300
0.7647	Intermediate Similarity	NPC320801
0.7647	Intermediate Similarity	NPC144258
0.7625	Intermediate Similarity	NPC175079
0.7619	Intermediate Similarity	NPC103486
0.7619	Intermediate Similarity	NPC100297
0.7614	Intermediate Similarity	NPC305039
0.759	Intermediate Similarity	NPC18955
0.7561	Intermediate Similarity	NPC478246
0.7561	Intermediate Similarity	NPC478247
0.7558	Intermediate Similarity	NPC478245
0.7558	Intermediate Similarity	NPC469948
0.7558	Intermediate Similarity	NPC90287
0.7531	Intermediate Similarity	NPC26504
0.7529	Intermediate Similarity	NPC105803
0.7529	Intermediate Similarity	NPC469561
0.75	Intermediate Similarity	NPC307298
0.75	Intermediate Similarity	NPC477372
0.75	Intermediate Similarity	NPC53454
0.75	Intermediate Similarity	NPC147438
0.75	Intermediate Similarity	NPC99308
0.75	Intermediate Similarity	NPC149237
0.7471	Intermediate Similarity	NPC51014
0.7471	Intermediate Similarity	NPC31564
0.7471	Intermediate Similarity	NPC145879
0.7471	Intermediate Similarity	NPC327115
0.7471	Intermediate Similarity	NPC474732
0.7471	Intermediate Similarity	NPC474778
0.7471	Intermediate Similarity	NPC474733
0.7471	Intermediate Similarity	NPC470345
0.7468	Intermediate Similarity	NPC144627
0.7444	Intermediate Similarity	NPC190442
0.7444	Intermediate Similarity	NPC248913
0.7442	Intermediate Similarity	NPC469569
0.7442	Intermediate Similarity	NPC473246
0.7442	Intermediate Similarity	NPC214043
0.7442	Intermediate Similarity	NPC85774
0.7419	Intermediate Similarity	NPC216904
0.7416	Intermediate Similarity	NPC310010
0.7416	Intermediate Similarity	NPC280833
0.7416	Intermediate Similarity	NPC326627
0.7416	Intermediate Similarity	NPC119416
0.7412	Intermediate Similarity	NPC193347
0.7412	Intermediate Similarity	NPC240302
0.7407	Intermediate Similarity	NPC475771
0.7407	Intermediate Similarity	NPC469669
0.7407	Intermediate Similarity	NPC469678
0.7386	Intermediate Similarity	NPC58063
0.7386	Intermediate Similarity	NPC220930
0.7386	Intermediate Similarity	NPC272039
0.7386	Intermediate Similarity	NPC475740
0.7386	Intermediate Similarity	NPC38885
0.7381	Intermediate Similarity	NPC474956
0.7381	Intermediate Similarity	NPC2482
0.7363	Intermediate Similarity	NPC229976
0.7356	Intermediate Similarity	NPC132629
0.7356	Intermediate Similarity	NPC197823
0.7356	Intermediate Similarity	NPC15838
0.7356	Intermediate Similarity	NPC323765
0.7342	Intermediate Similarity	NPC307176
0.734	Intermediate Similarity	NPC112753
0.734	Intermediate Similarity	NPC275439
0.7333	Intermediate Similarity	NPC129913
0.7333	Intermediate Similarity	NPC113393
0.7333	Intermediate Similarity	NPC472306
0.7326	Intermediate Similarity	NPC470047
0.7326	Intermediate Similarity	NPC470046
0.7326	Intermediate Similarity	NPC53733
0.7326	Intermediate Similarity	NPC168188
0.7326	Intermediate Similarity	NPC470015
0.7317	Intermediate Similarity	NPC263582
0.7317	Intermediate Similarity	NPC470525
0.7303	Intermediate Similarity	NPC471722
0.7303	Intermediate Similarity	NPC475001
0.7303	Intermediate Similarity	NPC474677
0.7303	Intermediate Similarity	NPC185059
0.7294	Intermediate Similarity	NPC282293
0.7294	Intermediate Similarity	NPC478262
0.7294	Intermediate Similarity	NPC121984
0.7294	Intermediate Similarity	NPC475833
0.7294	Intermediate Similarity	NPC475665
0.7294	Intermediate Similarity	NPC136150
0.7284	Intermediate Similarity	NPC470299
0.7283	Intermediate Similarity	NPC245972
0.7283	Intermediate Similarity	NPC212812
0.7283	Intermediate Similarity	NPC196485
0.7273	Intermediate Similarity	NPC222613
0.7273	Intermediate Similarity	NPC118648
0.7273	Intermediate Similarity	NPC475022
0.7273	Intermediate Similarity	NPC470346
0.7273	Intermediate Similarity	NPC20688
0.7273	Intermediate Similarity	NPC195640
0.7273	Intermediate Similarity	NPC72133
0.7273	Intermediate Similarity	NPC229717
0.7273	Intermediate Similarity	NPC94666
0.7262	Intermediate Similarity	NPC477371
0.7262	Intermediate Similarity	NPC472490
0.7262	Intermediate Similarity	NPC27817
0.7253	Intermediate Similarity	NPC174167
0.7253	Intermediate Similarity	NPC168027
0.7253	Intermediate Similarity	NPC470036
0.7253	Intermediate Similarity	NPC185936
0.7253	Intermediate Similarity	NPC131872
0.7253	Intermediate Similarity	NPC26865
0.725	Intermediate Similarity	NPC223187
0.7241	Intermediate Similarity	NPC58841
0.7241	Intermediate Similarity	NPC321187
0.7241	Intermediate Similarity	NPC161423
0.7241	Intermediate Similarity	NPC329043
0.7241	Intermediate Similarity	NPC227064
0.7241	Intermediate Similarity	NPC221758
0.7241	Intermediate Similarity	NPC475100
0.7241	Intermediate Similarity	NPC109512
0.7241	Intermediate Similarity	NPC59453
0.7237	Intermediate Similarity	NPC34622
0.7237	Intermediate Similarity	NPC474400
0.7229	Intermediate Similarity	NPC165711
0.7229	Intermediate Similarity	NPC316500
0.7222	Intermediate Similarity	NPC268406
0.7222	Intermediate Similarity	NPC31985
0.7222	Intermediate Similarity	NPC474245
0.7222	Intermediate Similarity	NPC26959
0.7222	Intermediate Similarity	NPC1015
0.7222	Intermediate Similarity	NPC186688
0.7222	Intermediate Similarity	NPC76879
0.7215	Intermediate Similarity	NPC139397
0.7209	Intermediate Similarity	NPC142683
0.7209	Intermediate Similarity	NPC151519
0.7209	Intermediate Similarity	NPC260956
0.7209	Intermediate Similarity	NPC469325
0.7209	Intermediate Similarity	NPC320514
0.7209	Intermediate Similarity	NPC328351
0.7204	Intermediate Similarity	NPC280725
0.7204	Intermediate Similarity	NPC295347
0.7191	Intermediate Similarity	NPC136548
0.7191	Intermediate Similarity	NPC93778
0.7191	Intermediate Similarity	NPC99909
0.7188	Intermediate Similarity	NPC124211
0.7176	Intermediate Similarity	NPC279667
0.7176	Intermediate Similarity	NPC472478
0.7174	Intermediate Similarity	NPC134826
0.7174	Intermediate Similarity	NPC233118
0.7174	Intermediate Similarity	NPC79117
0.7174	Intermediate Similarity	NPC263780
0.7174	Intermediate Similarity	NPC271652
0.7174	Intermediate Similarity	NPC12722
0.716	Intermediate Similarity	NPC474228
0.716	Intermediate Similarity	NPC303613
0.7159	Intermediate Similarity	NPC189311
0.7159	Intermediate Similarity	NPC123319
0.7159	Intermediate Similarity	NPC94531
0.7159	Intermediate Similarity	NPC470048
0.7159	Intermediate Similarity	NPC36350
0.7159	Intermediate Similarity	NPC473038
0.7159	Intermediate Similarity	NPC311702
0.7159	Intermediate Similarity	NPC179006
0.7159	Intermediate Similarity	NPC470574
0.7159	Intermediate Similarity	NPC29447
0.7159	Intermediate Similarity	NPC300985
0.7159	Intermediate Similarity	NPC474853
0.7159	Intermediate Similarity	NPC470223
0.7143	Intermediate Similarity	NPC62336
0.7143	Intermediate Similarity	NPC48010
0.7143	Intermediate Similarity	NPC275494
0.7143	Intermediate Similarity	NPC35574
0.7143	Intermediate Similarity	NPC189485
0.7143	Intermediate Similarity	NPC85173
0.7143	Intermediate Similarity	NPC471409
0.7143	Intermediate Similarity	NPC98897
0.7128	Intermediate Similarity	NPC328162

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC23778 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	2149
0.2-0.3	4230
0.3-0.4	1851
0.4-0.5	402
0.5-0.6	187
0.6-0.7	125
0.7-0.8	17
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8228	Intermediate Similarity	NPD3617	Approved
0.7907	Intermediate Similarity	NPD5737	Approved
0.7907	Intermediate Similarity	NPD6672	Approved
0.7805	Intermediate Similarity	NPD4695	Discontinued
0.7674	Intermediate Similarity	NPD5279	Phase 3
0.7647	Intermediate Similarity	NPD4197	Approved
0.7614	Intermediate Similarity	NPD6080	Approved
0.7614	Intermediate Similarity	NPD6904	Approved
0.7614	Intermediate Similarity	NPD6673	Approved
0.7558	Intermediate Similarity	NPD5329	Approved
0.7528	Intermediate Similarity	NPD5692	Phase 3
0.7471	Intermediate Similarity	NPD4694	Approved
0.7471	Intermediate Similarity	NPD5280	Approved
0.7471	Intermediate Similarity	NPD5690	Phase 2
0.7471	Intermediate Similarity	NPD6098	Approved
0.7444	Intermediate Similarity	NPD5693	Phase 1
0.7444	Intermediate Similarity	NPD6050	Approved
0.7444	Intermediate Similarity	NPD5694	Approved
0.7416	Intermediate Similarity	NPD4753	Phase 2
0.7412	Intermediate Similarity	NPD4223	Phase 3
0.7412	Intermediate Similarity	NPD4221	Approved
0.7391	Intermediate Similarity	NPD5695	Phase 3
0.7342	Intermediate Similarity	NPD4747	Approved
0.7273	Intermediate Similarity	NPD7521	Approved
0.7273	Intermediate Similarity	NPD7146	Approved
0.7273	Intermediate Similarity	NPD5330	Approved
0.7273	Intermediate Similarity	NPD7334	Approved
0.7273	Intermediate Similarity	NPD6684	Approved
0.7273	Intermediate Similarity	NPD6409	Approved
0.725	Intermediate Similarity	NPD5276	Approved
0.7241	Intermediate Similarity	NPD3665	Phase 1
0.7241	Intermediate Similarity	NPD3666	Approved
0.7241	Intermediate Similarity	NPD4786	Approved
0.7241	Intermediate Similarity	NPD3133	Approved
0.7234	Intermediate Similarity	NPD6083	Phase 2
0.7234	Intermediate Similarity	NPD6084	Phase 2
0.7215	Intermediate Similarity	NPD4137	Phase 3
0.7209	Intermediate Similarity	NPD3667	Approved
0.7204	Intermediate Similarity	NPD5654	Approved
0.7158	Intermediate Similarity	NPD5696	Approved
0.7125	Intermediate Similarity	NPD4691	Approved
0.7111	Intermediate Similarity	NPD6903	Approved
0.7111	Intermediate Similarity	NPD5208	Approved
0.7111	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4139	Approved
0.7093	Intermediate Similarity	NPD4692	Approved
0.7079	Intermediate Similarity	NPD4138	Approved
0.7079	Intermediate Similarity	NPD4690	Approved
0.7079	Intermediate Similarity	NPD5205	Approved
0.7079	Intermediate Similarity	NPD3618	Phase 1
0.7079	Intermediate Similarity	NPD4693	Phase 3
0.7079	Intermediate Similarity	NPD4688	Approved
0.7079	Intermediate Similarity	NPD4689	Approved
0.7073	Intermediate Similarity	NPD5733	Approved
0.7073	Intermediate Similarity	NPD4687	Approved
0.7053	Intermediate Similarity	NPD5959	Approved
0.7051	Intermediate Similarity	NPD3704	Approved
0.7051	Intermediate Similarity	NPD6108	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD3668	Phase 3
0.7033	Intermediate Similarity	NPD5328	Approved
0.7033	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5210	Approved
0.7021	Intermediate Similarity	NPD4629	Approved
0.6989	Remote Similarity	NPD5133	Approved
0.6957	Remote Similarity	NPD5207	Approved
0.6947	Remote Similarity	NPD4697	Phase 3
0.6947	Remote Similarity	NPD5221	Approved
0.6947	Remote Similarity	NPD5222	Approved
0.6947	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD4519	Discontinued
0.6889	Remote Similarity	NPD4623	Approved
0.6882	Remote Similarity	NPD6079	Approved
0.6875	Remote Similarity	NPD4755	Approved
0.6875	Remote Similarity	NPD5173	Approved
0.6867	Remote Similarity	NPD4058	Approved
0.6842	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4202	Approved
0.6809	Remote Similarity	NPD6399	Phase 3
0.6774	Remote Similarity	NPD4096	Approved
0.6742	Remote Similarity	NPD4788	Approved
0.6739	Remote Similarity	NPD4518	Approved
0.6737	Remote Similarity	NPD5282	Discontinued
0.6737	Remote Similarity	NPD6001	Approved
0.6735	Remote Similarity	NPD5286	Approved
0.6735	Remote Similarity	NPD4700	Approved
0.6735	Remote Similarity	NPD4696	Approved
0.6735	Remote Similarity	NPD5285	Approved
0.6733	Remote Similarity	NPD6402	Approved
0.6733	Remote Similarity	NPD7128	Approved
0.6733	Remote Similarity	NPD5739	Approved
0.6733	Remote Similarity	NPD6675	Approved
0.6709	Remote Similarity	NPD7341	Phase 2
0.6702	Remote Similarity	NPD5284	Approved
0.6702	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD4195	Approved
0.6667	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.663	Remote Similarity	NPD3573	Approved
0.6602	Remote Similarity	NPD6011	Approved
0.6602	Remote Similarity	NPD7320	Approved
0.6602	Remote Similarity	NPD6899	Approved
0.6602	Remote Similarity	NPD6881	Approved
0.66	Remote Similarity	NPD5225	Approved
0.66	Remote Similarity	NPD5226	Approved
0.66	Remote Similarity	NPD5211	Phase 2
0.66	Remote Similarity	NPD5224	Approved
0.66	Remote Similarity	NPD4633	Approved
0.6593	Remote Similarity	NPD1694	Approved
0.6538	Remote Similarity	NPD6014	Approved
0.6538	Remote Similarity	NPD6012	Approved
0.6538	Remote Similarity	NPD6013	Approved
0.6538	Remote Similarity	NPD6372	Approved
0.6538	Remote Similarity	NPD6373	Approved
0.6535	Remote Similarity	NPD4754	Approved
0.6535	Remote Similarity	NPD5174	Approved
0.6535	Remote Similarity	NPD5175	Approved
0.6506	Remote Similarity	NPD4789	Approved
0.6505	Remote Similarity	NPD6614	Approved
0.65	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD7290	Approved
0.6476	Remote Similarity	NPD7102	Approved
0.6476	Remote Similarity	NPD6883	Approved
0.6471	Remote Similarity	NPD5141	Approved
0.6456	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5091	Approved
0.6415	Remote Similarity	NPD8130	Phase 1
0.6415	Remote Similarity	NPD6617	Approved
0.6415	Remote Similarity	NPD6847	Approved
0.6415	Remote Similarity	NPD6869	Approved
0.6415	Remote Similarity	NPD6649	Approved
0.6415	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6650	Approved
0.6413	Remote Similarity	NPD1696	Phase 3
0.6408	Remote Similarity	NPD4767	Approved
0.6408	Remote Similarity	NPD4768	Approved
0.6408	Remote Similarity	NPD6008	Approved
0.6392	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7900	Approved
0.6392	Remote Similarity	NPD7748	Approved
0.6355	Remote Similarity	NPD8297	Approved
0.6355	Remote Similarity	NPD6882	Approved
0.6354	Remote Similarity	NPD7515	Phase 2
0.6286	Remote Similarity	NPD5168	Approved
0.6286	Remote Similarity	NPD4730	Approved
0.6286	Remote Similarity	NPD4729	Approved
0.6286	Remote Similarity	NPD5128	Approved
0.6263	Remote Similarity	NPD7732	Phase 3
0.625	Remote Similarity	NPD4756	Discovery
0.6222	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.622	Remote Similarity	NPD7331	Phase 2
0.6214	Remote Similarity	NPD6052	Approved
0.6207	Remote Similarity	NPD6942	Approved
0.6207	Remote Similarity	NPD7339	Approved
0.62	Remote Similarity	NPD7902	Approved
0.6196	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6868	Approved
0.6182	Remote Similarity	NPD6274	Approved
0.6168	Remote Similarity	NPD5250	Approved
0.6168	Remote Similarity	NPD5249	Phase 3
0.6168	Remote Similarity	NPD5169	Approved
0.6168	Remote Similarity	NPD4634	Approved
0.6168	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5248	Approved
0.6168	Remote Similarity	NPD5251	Approved
0.6168	Remote Similarity	NPD5135	Approved
0.6168	Remote Similarity	NPD5247	Approved
0.6154	Remote Similarity	NPD287	Approved
0.6147	Remote Similarity	NPD4632	Approved
0.6136	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD6317	Approved
0.6126	Remote Similarity	NPD6009	Approved
0.6111	Remote Similarity	NPD5216	Approved
0.6111	Remote Similarity	NPD5217	Approved
0.6111	Remote Similarity	NPD5215	Approved
0.6111	Remote Similarity	NPD5127	Approved
0.6092	Remote Similarity	NPD6924	Approved
0.6092	Remote Similarity	NPD4785	Approved
0.6092	Remote Similarity	NPD6926	Approved
0.6092	Remote Similarity	NPD4784	Approved
0.6071	Remote Similarity	NPD6313	Approved
0.6071	Remote Similarity	NPD5360	Phase 3
0.6071	Remote Similarity	NPD6335	Approved
0.6071	Remote Similarity	NPD6314	Approved
0.6071	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD4243	Approved
0.6047	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD5777	Approved
0.6044	Remote Similarity	NPD4748	Discontinued
0.6038	Remote Similarity	NPD6412	Phase 2
0.6026	Remote Similarity	NPD8779	Phase 3
0.6024	Remote Similarity	NPD4224	Phase 2
0.6018	Remote Similarity	NPD7100	Approved
0.6018	Remote Similarity	NPD7101	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data